Timberlake and JC Chasez were the two lead singers of the popular 1990s boy band 'N Sync.[7] The group formed in 1995, started its career 1996 in Europe, and hit it big in the United States in 1998 with the US release of its debut album *NSYNC, which sold 11 million copies.[8] The album included a number of hit singles such as "Tearin' Up My Heart." For the next two years, encouraged by similar developments with the Backstreet Boys, 'N Sync engaged in a lengthy legal battle with manager Lou Pearlman. Eventually the band signed with Jive Records.[9] 'N Sync released a long-awaited album, No Strings Attached, in March 2000, which became the fastest-selling album of all time with 2.4 million copies sold in its first week[10] and produced a #1 single, "It's Gonna Be Me". The release was followed by the band's third album, Celebrity, which held the title of the second-fastest selling album of all time. In 2002, after the completion of a Celebrity Tour and the release of "Girlfriend," the third single from Celebrity, the group decided to take time off, at which point Timberlake began work on his first solo album and the group went into a hiatus. In its lifetime, 'N Sync was internationally famous and performed at the Academy Awards,[11] the Olympics,[12] and the Super Bowl,[13] as well as selling more than 50 million copies worldwide,[14] becoming the third-best selling boy band in history.[15]

During late 1999, Timberlake made his acting debut in the Disney Channel movie Model Behavior, in which he played Jason Sharpe, a model who falls in love with a waitress after mistaking her for another model. It was released on March 12, 2000.[16]

As a member of 'N Sync, Timberlake developed into a major celebrity in his own right in addition to achieving respect as a musician, since he was the writer or co-writer of all three singles from Celebrity. The rise of his own stardom and the general decline in the popularity of boy bands led to a continuation of 'N Sync's hiatus, although the group has never officially disbanded. Band member Lance Bass has stated that he believes the group is finished,[17] and is openly critical of Timberlake's actions in his memoir Out of Sync. On the other hand, Chris Kirkpatrick remarked in August 2008 that the five remain friends, and he believed a reunion was possible:[18] he repeated that opinion in October 2009.[19] In September 2008, Bass also made conciliatory comments.[20]

In August 2002, after months of recording Justified, his debut solo album, Timberlake performed at the 2002 MTV Video Music Awards, where he premiered his first single, "Like I Love You," a sparse dance track produced by The Neptunes.[21] The song reached number eleven on the Billboard Hot 100.[22] Following the single, Timberlake released Justified on November 5, 2002.[23] The album sold fewer copies than previous 'N Sync efforts. It debuted at number two on the Billboard 200 album chart, selling 439,000 copies in its first week of release. It eventually went on to sell more than three million copies in the U.S. and more than seven million copies worldwide.[24] The album also received critical acclaim, thanks to its heavy R&B influence provided by hip-hop producers The Neptunes and Timbaland.[25] It spun off hits throughout late 2002 and 2003, including the top ten singles "Cry Me a River" and "Rock Your Body."[22] Timberlake supported the album by co-headlining the Justified/Stripped Tour with Christina Aguilera in the summer of 2003.[26] At the end of the year, Timberlake recorded a song entitled "I'm Lovin' It." It was used by McDonald's as the theme to its "I'm Lovin' It" campaign. The deal with McDonald's earned Timberlake an estimated $6 million. A tour entitled Justified and Lovin' It Live was included with the deal as well.[27] Timberlake was featured on Nelly's song, "Work It", which was remixed and included on Nelly's 2003 remix album.[28]

In February 2004, during the halftime show of the Super Bowl XXXVIII broadcast on the CBS television network, Timberlake performed with Janet Jackson before a television audience of more than 140 million viewers. At the end of the performance, as the song drew to a close, Timberlake tore off a part of Jackson's black leather costume in a "costume reveal" meant to accompany a portion of the song lyrics. According to CBS, "both Jackson and Timberlake had confirmed they planned it 'independently and clandestinely' without informing anyone."[29] Part of the costume detached, and Jackson's breast was briefly exposed.[30] Timberlake apologized for the incident, stating he was "sorry that anyone was offended by the wardrobe malfunction during the halftime performance of the Super Bowl...."[31] The phrase "wardrobe malfunction" has since been used by the media to refer to the incident and has entered pop culture.[32] As a result of the controversy, Timberlake and Jackson were threatened with exclusion from the 2004 Grammy Awards unless they agreed to apologize on screen at the event.[33] Timberlake attended and issued a scripted apology when accepting the first of two Grammy Awards he received that night (Best Pop Vocal Album for Justified and Best Male Pop Vocal Performance for "Cry Me a River").[34] He had also been nominated for Album of the Year for Justified, Record of the Year for "Cry Me a River", and Best Rap/Sung Collaboration for "Where Is the Love?" with The Black Eyed Peas.[35]

He continued to record with other artists. After "Where Is the Love?", he again collaborated with the Black Eyed Peas on the 2005 track "My Style" from their album Monkey Business.[40] When recording the 2005 single "Signs" with Snoop Dogg, Timberlake discovered a throat condition.[41]Nodules were subsequently removed from his throat in an operation that took place on May 5, 2005.[42] He was advised not to sing or speak loudly for at least a few months.[43] In the summer of 2005, Timberlake started his own record company, JayTee Records.[44]

Timberlake released his second solo album, FutureSex/LoveSounds, on September 12, 2006.[45] The album, which Timberlake created in 2005, debuted at number one on the Billboard 200 album chart, selling 684,000 copies its first week.[45] It is the biggest album for pre-orders on iTunes, and beat Coldplay's record for the biggest one-week sales of a digital album.[46] The album was produced by Timbaland and Danja (who produced a bulk of the album), will.i.am, Rick Rubin and Timberlake himself, and features guest vocals by Snoop Dogg, Three 6 Mafia, T.I. and will.i.am.[47] A studio representative described it as being "all about sexiness" and aiming for "an adult feel".[42]

The album's lead single, "SexyBack", was performed by Timberlake at the opening of the 2006 MTV Video Music Awards and reached number one on the Billboard Hot 100, where it remained for seven consecutive weeks.[48] "My Love", the album's second single, also produced by Timbaland and featuring rapper T.I., reached number one on the Hot 100, as did third single "What Goes Around.../...Comes Around Interlude". The song is reported to have been inspired by the break-up of his childhood friend and business partner, Trace Ayala, with actress Elisha Cuthbert.[49] In October 2006, Timberlake said that he would focus on his music career rather than his movie roles, specifying that leaving the music industry would be a "dumb thing to do at this point".[48] He was the special guest performer at the 2006 Victoria's Secret Fashion Show for being where he sang SexyBack. In January 2007, Timberlake embarked on the FutureSex/LoveShow tour. "Summer Love/Set the Mood Prelude" was the fourth U.S. single off the album, and the next single in the UK was "LoveStoned/I Think She Knows Interlude". The song "Give It to Me", a Timbaland single on which Timberlake guests with Nelly Furtado, reached the Hot 100 number-one spot.[50]

In February 2008, Timberlake was awarded two Grammy Awards. At the 50th Grammy Awards Ceremony, Timberlake won the Male Pop Performance Award for "What Goes Around...Comes Around", and the Dance Recording Award for "LoveStoned/I Think She Knows".[51]

In April 2007, Timberlake was seen entering a London studio with Madonna, thus confirming rumors that he was collaborating with her.[52] A song "4 Minutes", was first played by Timbaland at Philadelphia's Jingle Ball on December 17, 2007.[53] When released on March 17, 2008, "4 Minutes" was revealed to be a duet between Timberlake and Madonna, with backing vocals by Timbaland. It was lead single from Madonna's eleventh studio album Hard Candy, which featured four other song-writing collaborations with Timberlake. The single was an international hit, and topped the charts in Australia, Belgium, Canada, Denmark, Finland, Germany, Italy, Netherlands, Norway, Sweden, Switzerland and the United Kingdom, and reached the Top 5 in Austria, France, Ireland, Japan, New Zealand and the United States. Timberlake also appears in the music video, which was directed by Jonas & François. On March 30, 2008, Timberlake performed the song at Madonna's Hard Candy Promo Show at Roseland Ballroom in New York City.[54] On November 6, 2008, Timberlake performed the song with Madonna on the Los Angeles stop of her Sticky & Sweet Tour.[55]

Around June 2007 Timberlake co-wrote, produced and provided vocals for the songs "Nite Runner" and "Falling Down" for Duran Duran's album Red Carpet Massacre, released on November 13, 2007. "Falling Down" had been released as a single in the UK on the previous day.[56]

With the wrapping up of the FutureSex/LoveSounds tour of Australasia and the Middle East in November 2007, Timberlake resumed his movie career. Projects underway early in 2008 were starring roles in Mike Myers' comedy The Love Guru (released June 20, 2008) and Mike Meredith's drama The Open Road (released August 28, 2009). In March 2008 it was announced that he was be an executive producer in an American adaptation of the hit Peruvian comedy My Problem with Women for NBC.[58]

On November 20, 2008, TV Guide reported that Timberlake’s next single, "Follow My Lead", which also featured vocals by Timberlake’s protégée, former YouTube star Esmee Denters, would be available for exclusive download through MySpace. All proceeds would go to Shriners Hospitals for Children, a charity dedicated to improving pediatric care for sick children.[59]

In 2008 a collaboration between Timberlake and T.I., "Dead and Gone" featured on T.I.'s sixth studio album, Paper Trail, and was released as its fourth single late in 2009. In November 2008, it was confirmed that Timberlake would make a guest appearance and produce some tracks on R&B/pop singer Ciara's upcoming album Fantasy Ride due out May 5, 2009. Timberlake featured on Ciara's second single "Love Sex Magic", the video being shot on February 20, 2009.[60] The single became a worldwide hit, reaching the top ten in numerous countries and peaking at number one in several countries including Taiwan, India, and Turkey. The single is now nominated for Best Pop Collaboration with Vocals at the 52nd Grammy Awards.

Timberlake and his production team The Y's, along with Mike Elizondo, produced and co-wrote the song "Don't Let Me Down" for Leona Lewis's second studio album, Echo, released (in the US) on November 17, 2009.

Timberlake also co-wrote and performed on "Carry Out," the third single from Timbaland's album Shock Value II, released on December 1, 2009.[61]

In June 2012 Timberlake began working on a new album, The 20/20 Experience.[62] It was released on 19 March 2013.[63] The album came top of the Irish charts in the first week.[64] The single "Mirrors" was nominated for Best Pop Solo Performance at the 2014 Grammy Awards.[65]